Shehan Chandrasekera

Subscribe to Bits + Bips: https://bitsandbips.beehiiv.com/subscribe On this bundled episode of Bits + Bips, Unchained executive editor Steve Ehrlich digs into the less obvious risks shaping crypto returns, from DeFi yield to tax reporting. First, Sebastien Derivaux, co-founder of Steakhouse Financial, explains why chasing high yield can be dangerous, how institutional risk curation works onchain, and why the future of stablecoins won’t be limited to the US dollar. Then, Shehan Chandrasekera, CPA and Head of Tax Strategy at CoinTracker, breaks down what crypto investors need to know heading into 2026, including tax loss harvesting, the wash sale gray zone, hidden tax obligations in crypto ETFs, and why the new 1099-DA form won’t tell the full story. Host: Steve Ehrlich, Executive Editor at Unchained Guests: Shehan Chandrasekera, CPA, Head of Tax Strategy at CoinTracker Sebastien Derivaux, Co-Founder & Partner at Steakhouse Financial Timestamps: 🎬 0:00 Intro 🧾 1:10 How crypto fits into existing tax law 📅 2:14 What investors should be thinking about before year-end—and how tax loss harvesting works 🔁 4:54 The wash sale rule: Is it safe to use in crypto? ⚖️ 9:27 How upcoming legislation could change crypto taxes 💵 11:22 Stablecoins and taxes: Are there any special rules? 📊 13:47 The hidden tax complexity of trading crypto ETPs and ETFs 📄 16:39 What the new 1099-DA form is—and what it will (and won’t) tell the IRS 👀 22:31 The key things Shehan says crypto investors should watch closely 22:32 Intro 22:59 Understanding Steakhouse Financial and its growth rate 24:59 What “risk curation” actually means and why Steakhouse focuses on institutions 27:52 How Steakhouse vaults generate stablecoin yields 30:39 What risk curators can—and can’t—control in a decentralized environment 35:28 What recent volatility revealed about DeFi vaults and the collapse of Stream Finance 39:33 Whether “safe” high yield is even possible 41:33 The liquidity problem with tokenized credit funds onchain 49:48 How Steakhouse is positioning for the stablecoin boom 51:24 How stablechains like Tempo and Plasma could change the game 52:47 Why Steakhouse plans to integrate tokenized deposits 54:55 Steakhouse’s 2026 bet on non-USD stablecoins Learn more about your ad choices. Visit megaphone.fm/adchoices

Sebastien Derivaux

Co-founder

Steakhouse Financial

Shehan Chandrasekera

Head of Tax Strategy

CoinTracker

The IRS sparked a storm of controversy when it released proposed new rules for crypto transaction reporting earlier this year. The new rules seek to define who is considered a broker, what types of transactions need to get reported, and the kinds of digital assets that need to be included, but many in the industry consider them overly broad and ultimately unworkable.  Lawrence Zlatkin, VP of Tax at Coinbase, and Shehan Chandrasekera, Head of Tax Strategy at tax software firm CoinTracker, discuss the crypto industry’s specific objections to the proposed new rules, and what might be a better way forward. They also delve into how the regulations would apply to stablecoins and NFTs, potential blockchain-based solutions for the reporting requirements, and what the likely outlook and timeline for the proposals to come into effect are.   Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Music, or on your favorite podcast platform. Show highlights: What the newly proposed IRS regulations around crypto are and when they are likely to go into effect what entities qualify as a broker and why this may pose a problem what the implications for the industry are if these regulations were passed the number of additional reports the IRS is expecting to receive if these regulations are adopted how the regulations would apply to stablecoins and NFTs what the five types of brokers are under the proposed regulations and the three types that they exclude, according to Shehan the unprecedented amount of comments submitted what suggestions Coinbase and CoinTracker have in mind for better tax regulation why Lawrence thinks that DeFi exchanges should be treated the same as centralized ones whether people should have privacy concerns about the new proposals what some blockchain-based solutions for tax reporting are, such as attestation tokens what the next steps for the IRS proposed regulation are how long it will take to actually implement these regulations Thank you to our sponsors! LayerZero Popcorn Network Guests: Shehan Chandrasekera, Head of Tax Strategy at CoinTracker Lawrence Zlatkin, VP of Tax at Coinbase Links Previous coverage of Unchained on crypto taxes, with appearances from Shehan and Lawrence: Everything You Need to Know About Filing Your 2022 Crypto Taxes Your 2021 Crypto Taxes: How to Handle NFTs, DAOs, Airdrops and More Everything You Need to Know About Your 2020 Crypto Taxes  Why You Shouldn’t Trust Crypto Exchange Reports for Your Taxes The IRS Is Cracking Down on Crypto Taxes: What You Need to Know  Could the Bank Secrecy Act Harm Crypto? Coin Center Thinks So Infrastructure Investment and Jobs Act (117th Congress) Proposed rule: IRS proposed rule text: Gross Proceeds and Basis Reporting by Brokers and Determination of Amount Realized and Basis for Digital Asset Transactions U.S. Department of the Treasury, IRS Release Proposed Regulations on Sales and Exchanges of Digital Assets by Brokers CoinDesk: How the Crypto Industry Responded to the IRS Proposed Broker Rule Twitter thread from Ji Kim of Crypto Council for Innovation  CNBC: President Joe Biden to sign the bipartisan infrastructure bill⁠ into law—here's how crypto investors will be impacted IRS issues guidance, seeks comments on nonfungible tokens Coinbase first comment letter Coinbase second comment letter CoinTracker comment letter Learn more about your ad choices. Visit megaphone.fm/adchoices

Lawrence Zlatkin

VP of Tax

Coinbase

Shehan Chandrasekera

Head of Tax Strategy

CoinTracker

Lawrence Zlatkin, VP of Tax at Coinbase, and Shehan Chandrasekera, Head of Tax Strategy at CoinTracker, give a full accounting of everything U.S. crypto traders should be aware of as we inch closer to April 18. The two tax experts discuss the latest on how the IRS is approaching crypto taxation, going deep on everything from staking rewards to NFT royalties. Just a heads up: This interview is meant for informational purposes only and should not be construed as financial or tax advice. Show highlights: what’s new this year when it comes to reporting crypto transactions why staking is now firmly on the IRS’s radar how capital gains tax works for crypto the types of crypto transactions that are taxable as income the five situations where a crypto user incurs a taxable event the types of crypto activity that are not taxable what crypto holders can do to make tax time easier the IRS forms you need for various types of crypto transactions typical mistakes that crypto users make when it comes to filing their taxes why there’s not much you can do if you have assets stuck in Voyager, Celsius or other bankrupt crypto firms why you might consider arguing a “theft loss deduction” what to know about the Ethereum Merge as it relates to taxes things NFT creators should be aware of during tax time how the U.S. tax system can or cannot be applied to DeFi what tax forms you can expect to receive if you’re a Coinbase customer how corporations holding crypto may soon see favorable changes to current accounting rules why $5,000 is a key threshold for crypto donations Thank you to our sponsors! Crypto.com FTSE Halborn NYU Links Previous coverage of crypto taxes on Unchained: Your 2021 Crypto Taxes: How to Handle NFTs, DAOs, Airdrops and More Everything You Need to Know About Your 2020 Crypto Taxes  Why You Shouldn't Trust Crypto Exchange Reports for Your Taxes The IRS Is Cracking Down on Crypto Taxes: What You Need to Know  Guests: Shehan: Twitter CoinTracker Lawrence: Twitter Links: Digital Assets | Internal Revenue Service IRS CCA 202302012 (Crypto charitable donations) IRS CCA 202302011 (Coins which have substantially lost in value. Ex: Luna) MiCA – Overview of the New EU Crypto-Asset Regulatory Framework (Part 1) | HUB | K&L Gates CNBC: President Joe Biden to sign the bipartisan infrastructure bill⁠ into law—here's how crypto investors will be impacted S&P Global: What the US infrastructure bill means for cryptocurrency brokers and owners Learn more about your ad choices. Visit megaphone.fm/adchoices

Lawrence Zlatkin

VP of Tax

Coinbase

Shehan Chandrasekera

Head of Tax Strategy

CoinTracker

Two crypto tax experts, Shehan Chandrasekera, certified public accountant and head of strategy, Tax, at Cointracker, and John Cardone, senior director of Washington National Tax at RSM US LLP, explain everything crypto traders need to understand when filing taxes for 2021. Show topics: -the five types of transactions that constitute a taxable crypto event -how NFT taxes should be reported -why the sale of collectibles (NFTs) is taxed differently than the sale of crypto property (tokens) -what type of forms you might receive from crypto exchanges and why this information is usually incomplete -why the crypto provision in the infrastructure bill most likely won’t affect retail traders -why John wants a digital asset-specific 1099 form -how staking income will be taxed this year (and why this might change soon) -how to report taxes for… airdrops like ENS and SOS income earned via a play-to-earn game like Axie Infinity the sale of virtual land wrapping Bitcoin onto Ethereum rewards received via a crypto credit card -how to save money on taxes going forward -how Shehan and John think crypto taxes will evolve  -why the IRS listed a job posting for someone who could exploit crypto wallets Thank you to our sponsors! Crypto.com: https://crypto.onelink.me/J9Lg/unconfirmedcardearnfeb2021       Beefy Finance: https://beefy.finance   Bosonic: https://bosonic.digital/ Alchemy Pay:  https://alchemypay.org Become a Premium Bulletin Subscriber! Become a premium subscriber to my Bulletin newsletter, and you’ll get access   to:  a premium-only Discord group  premium-only interviews the opportunity to ask questions ️ the chance to weigh in on guests for Unchained and  whatever other future offerings we add to the mix Join today for $4.99/mo or $49.99/year!  Join now! Get a Signed Book Plate! Many of you have asked me how you can get a signed copy of the book. Here’s how: Pre-order the book, which you can do at bit.ly/cryptopians. Make a social media post about the book that includes the pre-order link, bit.ly/cryptoptians, or to the book on any bookseller of your choice. Send a copy of your receipt to hello@unchainedpodcast.com with the subject line, “signed book plate.” In the email, include a pdf of your receipt + a screenshot of or a link to your social media post + the address to which you’d like me to send the book plate + the name of who you’d like me to dedicate the book plate to. If you show a pre-order receipt that shows you bought more than one format of the book, such as an audiobook and a hardcover, you can get two signed book plates. Finally, if you sign up for the Bulletin premium subscription plus do all the above to get a signed book plate, you’ll also receive a POAP. Episode Links John Cardone ​​https://www.linkedin.com/in/john-cardone-436412b1/   Shehan Chandrasekera https://twitter.com/TheCryptoCPA Helpful Links Shehan’s tax guide: https://www.forbes.com/sites/shehanchandrasekera/2022/01/24/quick-guide-to-filing-your-2021-cryptocurrency--nft-taxes/?sh=d5c00f765f9d Staking rewards case: https://twitter.com/TheCryptoCPA/status/1489268205877035016  US Gov. job posting: https://sam.gov/opp/799a1650bd5349b6af4f646842999187/view  2022 Crypto Tax Guides CoinTracker: https://www.cointracker.io/blog/crypto-tax-guide CryptoTrader.Tax: https://cryptotrader.tax/blog/the-traders-guide-to-cryptocurrency-taxes Koinly: https://koinly.io/cryptocurrency-taxes/  ZenLedger: https://www.zenledger.io/guides/crypto-tax-us  Learn more about your ad choices. Visit megaphone.fm/adchoices

Shehan Chandrasekera

Head of Tax Strategy

CoinTracker

John Cardone

Senior Director of Washington National Tax

RSM US